methyl 3-O-allyl-2,4-di-O-benzyl-α-D-manno-hexodialdo-1,5-pyranoside | 126412-69-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3-O-allyl-2,4-di-O-benzyl-α-D-manno-hexodialdo-1,5-pyranoside
• 英文别名: (2S,3S,4S,5S,6S)-6-methoxy-3,5-bis(phenylmethoxy)-4-prop-2-enoxyoxane-2-carbaldehyde
• CAS: 126412-69-9
• 化学式: C₂₄H₂₈O₆
• 分子量: 412.483
• InChiKey: NIHHUMKVAOTGBZ-DJCPXJLLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  30.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  63.22
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl 3-O-allyl-2,4-di-O-benzyl-α-D-manno-hexodialdo-1,5-pyranoside 在 Wilkinson's catalyst bicyclo[2.2.2]octane-1,4-diamine 、 sodium hydride 、 magnesium 作用下， 以 四氢呋喃 、 乙醇 、 水 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 25.0h， 生成 (2R,3S,4S,5S,6S)-3,5-Bis-benzyloxy-2-((S)-1,2-bis-benzyloxy-ethyl)-6-methoxy-tetrahydro-pyran-4-ol
  参考文献：
  名称：

  Five monophosphates of methyl l-glycero-α-d-manno-heptopyranoside: synthesis, hydrolysis and migrations

  摘要：

  From suitably protected methyl alpha-D-mannopyranosides five methyl L-glycero-alpha-D-manno-heptopyranosides were synthesized by the one-carbon-atom chain elongation at C-6 and converted to five monophosphates (1-5) having the PO(OH)(2) group at O-2, -3, -4, -6 and -7. Compounds 1-5 were exposed to acidic and basic hydrolytic conditions used in lipopolysaccharide analysis and the products and their proportion were determined. Under acidic conditions, besides hydrolysis of the glycoside, migrations and hydrolytic cleavage of the phosphate residue were found. Under basic conditions the phosphates were stable. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00037-8
• 作为产物：
  描述：

  methyl 3-O-allyl-2,4-di-O-benzyl-α-D-mannopyranoside 在 草酰氯 、 二甲基亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 methyl 3-O-allyl-2,4-di-O-benzyl-α-D-manno-hexodialdo-1,5-pyranoside
  参考文献：
  名称：

  Five monophosphates of methyl l-glycero-α-d-manno-heptopyranoside: synthesis, hydrolysis and migrations

  摘要：

  From suitably protected methyl alpha-D-mannopyranosides five methyl L-glycero-alpha-D-manno-heptopyranosides were synthesized by the one-carbon-atom chain elongation at C-6 and converted to five monophosphates (1-5) having the PO(OH)(2) group at O-2, -3, -4, -6 and -7. Compounds 1-5 were exposed to acidic and basic hydrolytic conditions used in lipopolysaccharide analysis and the products and their proportion were determined. Under acidic conditions, besides hydrolysis of the glycoside, migrations and hydrolytic cleavage of the phosphate residue were found. Under basic conditions the phosphates were stable. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00037-8

文献信息

• Synthesis of two branched heptopyranoside- (L,D-Hepp)-containing trisaccharides of the inner-core region of Citrobacter PCM 1487
  作者：G. J. P. H. Boons、M. Overhand、G. A. van der Marel、J. H. van Boom

  DOI：10.1002/recl.19921110306

  日期：——

  4-di-O-benzyl-α-D-manno-hexodialdo-1,5-pyranoside gave a L-glycero-D-manno-heptopyranoside (L,D-Hepp) derivative having at C-7 the phenyldimethylsilyl function as a hydroxy-masking group. The L,D-Hepp) derivative was converted into two acceptors which could be applied successfully for the preparation of the trisaccharides L-α-D-Hepp)-(13)-O-[L-α-D-Hepp-(17)]-L-α-D-Hepp/-O-Me 20 and α-D-Glcp-(13)-O-[L-α-D-

  将（苯基二甲基甲硅烷基）氯化镁非对映异构地添加到甲基3 - O-烯丙基-2,4-二-O-苄基-α-D-甘露聚糖-己二醛-1,5-吡喃糖苷中得到L-甘油-D-甘露聚糖-在C-7具有苯基二甲基甲硅烷基的庚基吡喃糖苷（L，D-Hep p）衍生物是羟基掩蔽基团。的L，d-HEP p）衍生物转化成其可以成功地为三糖L-α-d-HEP的制备可以应用两个受体p） - （13） - ö - [L-α-d-Hepp- （17）] - L-α-d-HEP p / - ö -Me 20和α-d-GLC p - （13） - ö- [L-α-d-HEP p - （17）] - LD-HEP p -O-ME 26。
• Synthesis of a trisaccharide of the inner core region of Citrobacter PCM 187 lipopolysaccharide that contains l-glycero-α-d-manno-heptopyranosyl units
  作者：Geert J.P.H. Boons、Marc Overhand、Gijs A. van der Marel、Jacques H. van Boom

  DOI：10.1016/0008-6215(89)85198-5

  日期：1989.10
• BOONS, G. J. P. H.;OVERHAND, MARC;MAREL, GIJS A. VAN DER;BOOM, JACQUES H.+, CARBOHYDR. RES., 192,(1989) C. 1-4
  作者：BOONS, G. J. P. H.、OVERHAND, MARC、MAREL, GIJS A. VAN DER、BOOM, JACQUES H.+

  DOI：——

  日期：——